Stefanos Tsitsipas leads 7 to 1 over 8 singles meetings since 2021. Last meeting on 26/02/2025 at Dubai Duty Free Tennis Championships - Dubai.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 26/02/2025 | Dubai Duty Free Tennis Championships - Dubai | Round 2 | hard | Tsitsipas | 7-6(4) 2-6 6-4 |
| 12/04/2024 | Monte-Carlo Rolex Masters - Monte-Carlo | Quarter-final | clay | Tsitsipas | 6-4 6-2 |
| 03/11/2023 | Rolex Paris Masters - Paris | Quarter-final | indoor hard | Tsitsipas | 6-3 6-4 |
| 28/03/2023 | Miami Open - Miami | Round 4 | hard | Khachanov | 7-6(4) 6-4 |
| 26/01/2023 | Australian Open - Melbourne | Semi-final | hard | Tsitsipas | 6-7(2) 4-6 7-6(6) 3- |
| 12/05/2022 | Internazionali BNL d'Italia - Rome | Round 3 | clay | Tsitsipas | 6-4 0-6 3-6 |
| 12/08/2021 | Rogers Cup - Toronto | Round 3 | hard | Tsitsipas | 3-6 2-6 |
| 05/03/2021 | ABN AMRO World Tennis Tournament - Rotterdam | Quarter-final | indoor hard | Tsitsipas | 6-4 3-6 5-7 |
| hard | Khachanov 1 - 3 Tsitsipas |
| clay | Khachanov 0 - 2 Tsitsipas |
| indoor hard | Khachanov 0 - 2 Tsitsipas |
| 2025 | Khachanov 0 - 1 Tsitsipas |
| 2024 | Khachanov 0 - 1 Tsitsipas |
| 2023 | Khachanov 1 - 2 Tsitsipas |
| 2022 | Khachanov 0 - 1 Tsitsipas |
| 2021 | Khachanov 0 - 2 Tsitsipas |
177 wins, 124 losses since 2021 (58.8%).
Last matches: V V D D D
256 wins, 122 losses since 2021 (67.7%).
Last matches: V V V D V
Stefanos Tsitsipas leads 7 to 1 over 8 singles meetings since 2021.
On 26/02/2025, at Dubai Duty Free Tennis Championships - Dubai (Round 2): Stefanos Tsitsipas won 7-6(4) 2-6 6-4.